Strange Bedfellows
by The Lilac Elf of Lothlorien
Summary: Grief-or Purgatory-can change a person as Sam and Dean soon find out. When they reunite, things get more than a bit complicated. Dean is bedding with an old enemy and Sam is sleeping with one of Dean's exes. AU of Season 8!
1. Unlikely Meetings

AUTHOR'S NOTES: So I got to thinking about the first several episodes of season 8 of Supernatural-BTW, am I the only one who totally digs the new opening graphic?-and I thought about what might have happened if Sam and Dean had met different people after the events at the end of season 7.

STORY SUMMARY: After season 7, Sam just wants to walk away from being a hunter, but a face from the past draws him back in. Meanwhile, Purgatory has a strange way of making friends out of enemies and Dean ends up with a most unexpected lover.

* * *

SUPERNATURAL: Strange Bedfellows

_Purgatory_

The Vampire had Dean Winchester pinned down on the ground and with one hand he tried to break the monster's grip while with the other he tried to reach for his homemade blade.

But just as Dean's brain started the usual pre-death 'life before his eyes' flash, the vamp let go and the hunter saw the monster's head roll away. Swiftly getting to his feet, Dean grabbed his weapon and looked at the hooded figure, holding a weapon of their own. "Who are you?" he demanded. Allies were rare here in Purgatory and usually just turned right around and tried to kill you. All the more reason Dean was reluctant to trust the stranger that had just saved his hide.

The figure was still and silent for a moment before she raised a hand and pulled back the hood, revealing herself to be a young blonde woman. She smiled when she saw Dean's look of incredulous recognition and she said, "I'm the girl that just saved your ass."

Dean couldn't speak for a moment but when he finally found his voice, he could only say one word. "Ruby?"

"You were expecting someone else?" Ruby replied as she headed off into the dense woods, gesturing for the hunter to follow her. The pair traveled for several hours in silence until coming to a cave. Once inside, Ruby built a fire and sat down on the ground.

"How'd you find me?" Dean asked, curiously, as he slowly sat down as well. "For that matter, how did you know I was here at all?"

Ruby gave a dry laugh at that. "I heard there was a human in Purgatory and you and Sam were the only humans I could think of stupid enough to end up here."

Dean shifted uncomfortably as he thought of Sam. He hoped his brother was alright. "Yeah, well…" he said, not really wanting to get into talking about it. "That's what I get for standing too close to exploding Leviathans."

The demon paused at that and she seemed to be lost in thought for a few moments. "Look, I know I'm the last person you want help from," she said after a while. "—and I don't blame you if you don't want to trust me. But there might be a way to get you out of here."

That caught Dean's attention and he straightened up. "Where?"

Ruby could tell Dean wanted to get going but she could also tell that it had been a long time—months, likely—since the hunter had slept a full night. "We'll set off in the morning. There's a stream about a day's journey from here. We can follow it to where we need to go." When Dean started to argue, she pressed on. "Get some sleep, Dean." Nodding at the warding sigils painted all around the cave walls Ruby added, "Nothing's getting in here. It's safe."

It had been so long since Dean had felt safe anywhere that it was hours before he was finally able to close his eyes and drift off, listening to the sounds of the crackling fire.

* * *

_Coatesville, Pennsylvania_

Even though he had resolved to give up hunting, Sam Winchester still ran towards the sounds of a violent fight as he walked down the street. Hurrying into the fray, Sam helped the young woman as she battled the demons and when he'd stabbed the last one with the knife he'd gotten from the demon, Ruby, he finally turned to the girl whose eyes lit up with surprise.

"Sam!"

It took Sam a moment or two to recognize the girl and when he did finally place her, he was even more surprised. "Jamie? What, you…You hunt demons now?"

Jamie grinned as she led Sam behind an alley where her car was parked. "Well, after a shapeshifter decides he wants you as his bride, working as a bartender gets kinda boring, you know?" She watched Sam who seemed to be reluctant to let her out of his sight. "Look, I've been doing this for a couple years now." When Sam didn't appear to be reassured, she smiled warmly. "I'll be fine, Sam. Promise. I'm a big girl—I can take care of myself."

But Sam was still unconvinced and after a moment or two he said, "I'll be right behind you."

Jamie went up on tiptoe so she could give the younger Winchester a lingering kiss on the cheek. "Whatever you say, my white knight."

The kiss burned on his cheek as Sam watched Jamie get into her car. There was a big part of him that wanted so much to be with the rookie hunter but remembering the relationship with Jamie'd had with Dean made his heart ache.

xxxxxxxxx

Jamie Wilkinson had grown up in her grandparents' house since her parents had disappeared when she was 6 years old. The house was old—one of the first houses built in the town, in fact—but it was still as cared for as it had been all those years ago.

The house wasn't very big but it had been enough for the three people and Jamie had lived here all the way through college. When she'd graduated, her grandparents had given her the house before moving down to Georgia.

Opening the front door, Jamie smiled to herself as she heard an old engine rumble behind her. Turning to see Sam parking, she couldn't help but noticing how the man seemed to be hurting and she wondered where Dean was. Was Dean's absence the reason for the pain in Sam's eyes as he joined her?

Once the two were inside, Jamie went into the kitchen and started cooking. Sam sat in the dining room, pulling out his laptop from his bag and setting it up at the table.

After half an hour, Sam looked up at the kitchen as a wonderful aroma started wafting out. "What smells so good?" he asked as Jamie came out for a moment holding two bottles of beer.

Handing one of the bottles over to Sam, Jamie replied, "Lemon pepper shrimp, Italian sausage, sautéed mushrooms, and linguine. I'm just waiting on the garlic bread."

Sam just nodded as he turned his attention back to his computer. But after a moment, he felt a gentle hand on his arm and looked up to see Jamie's soft gaze looking at him with concern. Knowing that she wanted to know what was going on, Sam felt something inside of him start to break. "Dean's gone," he just said, quietly.

"Oh, Sam," Jamie sighed, sympathetically as she squeezed Sam's arm in comfort.

* * *

A/N: Next chapter I'll be re-writing 'We Need To Talk About Kevin' to include Jamie and Ruby.


	2. Reunions

AUTHOR'S NOTES: So before I start with the canon stuff, I just wanted to put in an extended reunion scene.

Also, instead of the canon dog, I am replacing him with my own 6-year-old Australian Shepard, Abby. So all of the dog's actions in this story are what my dog does.

* * *

_11 Months Later_

_100-Mile-Wilderness, Maine_

By some miracle, Dean Winchester found himself standing in the middle of a forest next to Ruby and Castiel who looked around, nervously. "Did it work?" Dean asked, his right hand gripping his gun tightly. "Are we back?"

Ruby nodded, happily. She recognized the stars and constellations as she looked up and felt a wave of relief. She was out of Purgatory!

After getting killed by Sam 5 years ago, Ruby had been sent—not to Hell as was usual with demon deaths—but to Purgatory where she'd spent the bulk of her time hiding from monsters that seemed set on ripping her apart piece by piece.

And then she'd heard rumors spreading like wildfire about an angel opening a gateway to Purgatory. Not just an angel, though, but also Crowley who had taken the title King of Hell. He was looking for a way into Purgatory and had been about to open his own gateway when his angelic counterpart—Castiel—had beaten him to it.

Standing next to the demon and his best—well, only friend, really—Castiel felt both nervous and free. He took a deep breath of cool night air and enjoyed the scent of grass and pine—a serious contrast to the constant stench of blood and death that was pervasive it Purgatory. They were free…

Dean took a bit longer before his muscles eased. Before he could stop and think, he grabbed Ruby, pulling her into a passionate kiss. He laughed for the first time in a long, long time and he spun his girlfriend/lover around before kissing her again.

"We should seek shelter," Castiel said, looking around the woods. "Then we need to find Sam and…" The angel stopped when he heard a dual 'thump' behind him followed by quiet, muffled laughter and passionate moaning. Glancing at his companions, Cas quickly looked away as he saw Ruby and Dean pulling each other's clothes off. "I will go see where we are," he said, even though he was willing to bet that neither Dean nor Ruby heard him.

xxxxxxxxx

As the sun started to rise over the forest, Dean opened his eyes and smiled as he felt Ruby's arms around him. God, he couldn't believe that he thought that was a good thing. But as the demon helped him track down Cas, she'd also helped Dean hold on to his humanity even as Purgatory tried to bleed it out of him.

When all leads to the angel had dried up, Dean had screamed in pain and rage before going out on his own amidst Ruby's protests. He'd gone out looking for whatever fights he could find and when Ruby found him and tried to lead him back to the safety of the cave, he'd started fighting her.

Dean had thrown punches, and tried to kill the demon but Ruby had deflected most of the blows. When the older Winchester had fallen to the ground in exhaustion, Ruby had just knelt down next to him, trying to be comforting.

The pair had started off with the shakiest trust—especially where Dean was concerned—but every day spent together in Purgatory seemed to push hunter and demon closer together.

"You know you and Sam have the same habits?" Ruby said, a smirk on her face as she gathered her clothes. When she caught Dean's puzzled look, she grinned. "Sam always had that same reflective look the morning after we—"

"Yeah, don't…don't finish that sentence," Dean warned as he also gathered his clothes. After a minute or two, he turned to Ruby and said, "Come on. Let's go."

* * *

_Coatesville, PA_

Sam woke to the aromas of sausage frying and after getting up, he also smelled freshly brewed coffee. Hearing a piercing, high-pitched bark, Sam grinned as a blue merle Australian shepard jumped up to give him a doggy kiss on the face. "Down, Abby," Sam said, even though he smiled as he chastised the dog.

The Aussie had been an unexpected addition to the couple of Sam and Jamie. 7 months ago, the dog had shown up on a very cold night, sleet and rain falling hard. The poor animal was half-frozen and very thin and her fur was dirty and matted.

But after a trip to a local pet groomer and only a few weeks of TLC, Abby was happy and bouncy with a soft coat and a great deal of affection for the two humans who had rescued her.

Hearing the front door open, Sam tensed and he watched Abby who trotted out of the room and towards the door before letting out a loud bark alerting her humans to an unexpected arrival. "Abby?" Sam called, hurrying to the door when he heard the dog growling.

"Down, puppy," a familiar voice said to Abby as Sam got to the door. Seeing his brother, Dean smiled and hugged his brother who was dumbfounded to see his older brother alive. "So is this your girlfriend?" After letting go of Sam and bending down, Dean started rubbing the dog's ears. "Hey, girl. I'm Dean."

"Dean… what the Hell are you doing here?" Sam exclaimed, still in absolute shock that his brother was alive. "Where have you been?"

"Purgatory," Dean replied, simply, as he stood. Catching the aromas of coffee, sausage and cinnamon, he grinned and entered the living room saying, "Man, I'm starved. What's for breakfast?"

But Sam turned to stare at his brother's back as he said, "Wait, Dean, I—"

"Hello, Sam," Castiel said as he, too, entered the house. He wore jeans and a faded t-shirt and the old worn tan trenchcoat he always wore, although the coat looked like it had been through a war. Which—if Cas had been in Purgatory with Dean—he probably had.

"Cas?" Sam asked, looking confused. "How did—?"

"Long story," Ruby replied, bringing up the rear. Her blonde hair was back in a ponytail and she wore faded jeans, a long-sleeved shirt, and a leather jacket. Smiling at Sam she said, "Long time, no see."

Sam had moved from confused to completely flabbergasted. This was… His head spun and he looked from his brother to the angel to the demon.

Jamie looked equally confused as she came out of the kitchen and saw Dean and two others sitting at the dining room table. Turning to Sam, she asked, "Sam, what's going on?"

Seeing that Sam and Jamie—Hey, who said that Dean didn't remember his old girlfriends?—wanted answers, Dean replied, "How about this? We all eat, we talk…I'll tell our story if you tell yours. Deal?"

"Sure," Jamie agreed, heading back to the kitchen.

Ruby got up quickly to help Sam's girlfriend, knowing that the Winchesters probably needed a few moments alone.

"Seriously?" Sam hissed, angrily, under his breath as soon as the demon was out of the room. "Ruby? What the fuck are you thinking? I mean, did you just forget everything that we went through because of her? Are you insane?"

"Me?" Dean replied, keeping his voice equally low. "Did you forget that I slept with Jamie, too? And now you're hooking up with her?" He glanced at the kitchen before turning back to his brother. "Look, Sammy… You weren't there, okay? I mean, I… I never meant for any of it to happen. Ruby and I ended up in the same foxhole, and… I depended on her, Sam. I mean she always had my back, she helped me find Cas."

Sam let out a long sigh, knowing what his brother was saying. At the same time, he remembered only too painfully what Ruby had done to him—the demon blood, tricking him into breaking the final seal to free Lucifer… "I'm not going to trust her," he said, flatly.

"Dude, I'm not asking you to!" Dean said quietly, checking to see that the ladies weren't listening to the conversation. "Just… don't kill her, okay? Trust her or don't, I don't care. Just… don't kill her, alright?"

x

In the kitchen, Jamie couldn't help but feel awkward as she kept sneaking glances at Sam and Dean.

"You've never been in the middle of a Winchester argument, have you?" Ruby asked, knowingly. When Jamie gave her a look, Ruby smiled. "Best thing to do is just stay out of it," she advised. After a moment, she added, "Could be worse. At least your history with the boys is way better than mine."

Jamie considered that for a moment but she didn't say anything. After getting the whole story about what had happened since the last time she had seen the Winchesters, she had just looked at Sam for the longest time, noticing that he looked so much older than when she'd met him. And when Sam had started talking about Ruby and the whole mess with the demon blood, Jamie wished she could have killed the bitch herself for causing the Winchesters so much pain.

And now said bitch was in her kitchen.

"Let me be perfectly clear," Jamie said, her tone even as she stared at Ruby. "After everything you've put Sam and Dean through, if you even think of double-crossing them, I promise you're not going to like what happens next."

Ruby didn't back down but she didn't reply either. Instead, she grabbed the pan of cinnamon rolls cooling on the counter and headed back to the dining room and set the pan down in the middle of the table. When she sat down and took a sip from Dean's coffee cup, Ruby hissed in pain. "What the Hell?" she snapped, angrily.

"Oops," Jamie said without a trace of remorse. "Sorry. Forgot to tell you—I blessed the waterlines 4 years ago."

Ruby glared at Jamie who just smiled in return. "Fine. Got any beer?"

"Just from a local brewery that blesses each bottle they sell me," the hunter replied.

Sam and Dean exchanged a look before turning their attention to Jamie. "You have your beer blessed?" Dean asked.

"And every other liquid that I bring in here," Jamie said, nodding. "I may be relatively new on this, but I'm not an idiot."

There was a long awkward silence while the group ate with Jamie and Sam occasionally giving Abby tidbits. The dog tried resting her head on Dean's leg, giving the human the full extent of her blue eyes, but Dean seemed strangely immune. After a few moments, she gave a soft whine. Then another whine. When Dean still ignored her, Abby lifted her head from the human's leg before pawing his leg, hard, and giving a loud, high-pitched—almost ear-piercing—bark.

"Jeez!" Dean exclaimed, glaring at the dog. "I heard ya the first time!"

'Well, you didn't ACT like you heard me,' was the look the dog gave.

Dean glared at Abby why just looked right back at him. The two were locked in a staring contest for nearly two minutes before Abby jumped up to lick Dean on the face. "You're gonna pay for that, puppy," Dean promised as he wiped dog spit off his face with one hand.

Abby just grinned and gave the human a look that just said, 'Bring it on.'


End file.
